EP4237847A1 - Procédés d'identification de carburant d'hydrocarbures - Google Patents

Procédés d'identification de carburant d'hydrocarbures

Info

Publication number
EP4237847A1
EP4237847A1 EP21815074.6A EP21815074A EP4237847A1 EP 4237847 A1 EP4237847 A1 EP 4237847A1 EP 21815074 A EP21815074 A EP 21815074A EP 4237847 A1 EP4237847 A1 EP 4237847A1
Authority
EP
European Patent Office
Prior art keywords
fuel
marker compound
gasoline
fluorescence intensity
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP21815074.6A
Other languages
German (de)
English (en)
Inventor
Scott D. Schwab
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Afton Chemical Corp
Original Assignee
Afton Chemical Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Afton Chemical Corp filed Critical Afton Chemical Corp
Publication of EP4237847A1 publication Critical patent/EP4237847A1/fr
Pending legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/26—Oils; Viscous liquids; Paints; Inks
    • G01N33/28—Oils, i.e. hydrocarbon liquids
    • G01N33/2835—Specific substances contained in the oils or fuels
    • G01N33/2882—Markers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/003—Marking, e.g. coloration by addition of pigments
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • C10L1/1855—Cyclic ethers, e.g. epoxides, lactides, lactones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
    • C10L1/2283—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N1/00—Sampling; Preparing specimens for investigation
    • G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
    • G01N1/40—Concentrating samples
    • G01N1/4055—Concentrating samples by solubility techniques
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
    • C09B11/08—Phthaleins; Phenolphthaleins; Fluorescein
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
    • C10L2200/0415—Light distillates, e.g. LPG, naphtha
    • C10L2200/0423—Gasoline
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
    • C10L2200/0438—Middle or heavy distillates, heating oil, gasoil, marine fuels, residua
    • C10L2200/0446—Diesel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/16—Tracers which serve to track or identify the fuel component or fuel composition
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/36—Applying radiation such as microwave, IR, UV
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/54—Specific separation steps for separating fractions, components or impurities during preparation or upgrading of a fuel
    • C10L2290/544—Extraction for separating fractions, components or impurities during preparation or upgrading of a fuel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/60—Measuring or analysing fractions, components or impurities or process conditions during preparation or upgrading of a fuel
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N1/00—Sampling; Preparing specimens for investigation
    • G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
    • G01N1/40—Concentrating samples
    • G01N1/4055—Concentrating samples by solubility techniques
    • G01N2001/4061—Solvent extraction
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material

Definitions

  • fuel companies often include within their branded fuel unique additive packages containing, for instance, select amounts of detergents, dispersants, friction modifiers, and many other compounds to achieve desired quality and performance. Consumers may rely upon the branded fuel and their advertised quality to assure that the product being purchased meets desired expectations. [0003] Fuel companies, in some circumstances, often lose control of their product when it reaches the gas dealer or fueling station. In an effort to increase revenue or profits, end use providers could dilute a branded product with a lower quality one.
  • FIGS.1 to 5 are plots of additive treat rate versus fluorescence intensity of a marker compound in water phase.
  • the method includes obtaining a sample of a hydrocarbon fuel containing a measureable amount of a marker compound, the marker compound having a fluorescence intensity and at least partially soluble in water; combining the hydrocarbon fuel with water, and mixing the fuel and water mixture; after the mixing, allowing the fuel and water mixture to separate into a water phase and a fuel phase to at least partially extract the marker compound into the water phase; and subjecting the water phase to light having a wavelength of 250 nm to 800 nm and observing the fluorescence emitted from the marker compound in the water phase.
  • the observing includes measuring a fluorescence intensity of the water phase and determining a concentration of the marker compound in the fuel based on the fluorescence intensity of the water phase with the at least partially extracted maker compound therein relative to a baseline fluorescence intensity of the water phase without the marker compound.
  • the fuel is selected from gasoline or diesel; and/or wherein the fuel is gasoline containing low alcohol (e.g., methanol, ethanol, or propanol); and/or wherein the gasoline contains at least about 2 volume percent ethanol; and/or wherein the fuel includes a fuel performance additive selected from the group consisting of detergents, antioxidants, carrier fluids, metal deactivators, corrosion inhibitors, biocides, antistatic additives, drag reducing agents, demulsifiers, emulsifiers, dehazers, anti-icing additives, antiknock additives, anti-valve-seat recession additives, lubricity additives, surfactants, combustion improvers, or combinations thereof; and/or wherein the detergent is selected from the group consisting of Mannich reaction products formed by condensing a long-chain aliphatic hydrocarbon-substituted phenol or cresol with an aldehyde and an amine; long chain aliphatic hydrocarbons having
  • a gasoline composition is also provided by the present disclosure.
  • the gasoline composition includes a major amount of gasoline including at least about 2 volume percent ethanol; a gasoline performance additive including an additive selected from the group comprising detergents, antioxidants, carrier fluids, metal deactivators, corrosion inhibitors, biocides, antistatic additives, drag reducing agents, demulsifiers, emulsifiers, dehazers, anti-icing additives, antiknock additives, anti-valve-seat recession additives, lubricity additives, surfactants, combustion improvers, or combinations thereof; about 0.01 to about 100 parts per billion of a marker compound having a fluorescence intensity; and a partition ratio of the marker compound between water and gasoline of at least about 0.1.
  • the gasoline composition of the previous paragraph may be combined with optional features and embodiments in any combination thereof.
  • These optional features or embodiments may include: wherein the gasoline includes about 25 to about 1000 ptb (pounds per thousand barrels) of the fuel performance additive in the gasoline; and/or wherein the marker compound having a fluorescence intensity has a structure of Formula I: wherein R 1 and R 2 are independently hydrogen, a linear or branched alkyl group, or R 1 and R 2 may join to form a cyclic group or an aromatic group; n is an integer of 1 or 2; and each R 3 is hydrogen, a halogen atom, or a linear or branched C1 to C12 alkyl group; and/or wherein the marker compound having a fluorescence intensity has a structure of Formula II: (Formula II); and/or wherein the marker compound having a fluorescence intensity has a structure of Formula III: (Formula III) and wherein each R 4 is independently a C1 to C10
  • the present disclosure provides methods for identifying a hydrocarbon fuel, such as the presence and/or amounts of marker compounds having a fluorescence intensity and, through correlation, also identify the presence and/or amounts of additive package(s) within the hydrocarbon fuel.
  • the methods herein include first obtaining a sample of a hydrocarbon fuel containing a measureable amount of a marker compound.
  • the marker compound has a fluorescence intensity and is at least partially soluble in water.
  • the hydrocarbon fuel with the marker compound therein is combined with water to form a fuel and water mixture. The mixture is agitated to facilitate contact between the water and fuel.
  • the fuel and water are allowed to separate into a water phase and a fuel phase to at least partially extract the marker compound into the water phase. Then, a fluorescence intensity of the water phase is measured and a concentration of the marker compound in the fuel (and thus, a concentration of the additive package in the fuel by correlation) is determined based on the fluorescence intensity of the water phase with the at least partially extracted maker compound therein. In some instances, the concentration may be corrected relative to a baseline fluorescence intensity of water or the water phase without the marker compound.
  • the hydrocarbon fuel may include diesel, biodiesel, gasoline (also known as petrol), alcohol-based fuels, alcohol-blended fuels, or mixtures thereof.
  • an alcohol- blended fuel may include a fuel, such as gasoline, blended with ethanol as described more below.
  • a fuel such as gasoline
  • ethanol herein is meant ethyl alcohol, the chemical compound C 2 H 5 OH. This can arise in or be provided in many qualities or grades, such a commercial fuel grade, as well as pure or reagent grade ethanol, and can be derived from any source such as but not limited to petroleum refinery streams, distillation cuts, and bio-derived (e.g. bioethanol such as from corn).
  • the fuel is gasoline or diesel.
  • the fuel is gasoline and, preferably, gasoline with an amount of ethanol therein.
  • the gasoline may contain at least about 2 volume percent ethanol (in other approaches, at least about 5 volume percent ethanol, at least about 10 volume percent ethanol, at least about 15 volume percent ethanol, at least about 20 volume percent ethanol, or at least about 25 volume percent ethanol and, in some approaches, less than about 50 volume percent ethanol, less than about 40 volume percent alcohol, less than about 30 volume percent ethanol, less than about 25 volume percent ethanol, or less than about 20 volume percent ethanol).
  • the fuel includes one or more fuel performance additives selected from the group consisting of detergents, antioxidants, carrier fluids, metal deactivators, corrosion inhibitors, biocides, antistatic additives, drag reducing agents, demulsifiers, emulsifiers, dehazers, anti-icing additives, antiknock additives, anti-valve-seat recession additives, lubricity additives, surfactants, combustion improvers, or combinations thereof.
  • the marker compound is at least partially soluble in water and, in some approaches, stable within the fuel and additive composition wherein the marker compound does not react with the hydrocarbon fuel and/or additives within the hydrocarbon fuel.
  • Solubility between phases may be determined through a partition ratio.
  • the partition ratio is defined herein as the equilibrium concentration of the marker compound in the water phase divided by the equilibrium concentration of the marker compound in the fuel phase.
  • a partition ratio of the marker compound between the water and the fuel phases herein may be at least about 0.1, at least about 0.2, at least about 0.3 at least about 0.4, at least about 0.5, at least about 1, at least about 2, at least about 5, at least about 8, at least about 10, at least about 15, or even at least about 20 and less than 30, less than 25, less than 20, less than 15, or even less than 10.
  • Partition ratios greater than 1 mean the marker compound is more soluble in water than fuel and partition ratios less than one mean the marker compound is partially soluble in water.
  • the selected marker compound demonstrates a linear relationship or correlation between the fluorescence intensity and the concentration of marker compound in the fuel within a concentration range of the marker compound of interest in the fuel.
  • approaches of the methods herein include the fuel having about 0.01 to about 100 parts per billion (ppb) of the marker compound, in other approaches, about 0.5 to 70 ppb, about 1 to about 50 ppb, about 1 to about 30 ppb, about 1 to about 20 ppb, about 1 to about 15 ppb, or about 1 to about 10 ppb of the marker compound (or other ranges therewithin).
  • the relationship between the fluorescence intensity of the marker compound and concentration of the marker compound is linear within such amounts of the marker compounds in the fuels herein.
  • the marker compound having a fluorescence intensity suitable for the methods herein has a structure of Formula I: (Formula I, Fluorescein) wherein R 1 and R 2 are independently hydrogen, a linear or branched alkyl group, or R 1 and R 2 may join to form a cyclic group or an aromatic group; n is an integer of 1 or 2; and each R 3 is hydrogen, a halogen atom, or a linear or branched C1 to C12 alkyl group [00017]
  • the marker compound having a fluorescence intensity suitable for the methods herein has a structure of Formula II: (Formula II, Rhodamine 101)
  • the marker compound having a fluorescence intensity suitable for the methods herein has a structure of Formula III: (Formula III, Rhodamine B
  • marker compounds of Formula I, II, and/or III have surprisingly demonstrated the desired water solubility, partition ratio, stability in typical additive packages, and stability in hydrocarbon fuels having an additive package therein.
  • the marker compounds herein are free of non-cyclic ester groups and, in some approaches, free of non-cyclic ester groups means that hydroxyl groups on marker compound ring structures are not esterified as further shown by the marker compound structures herein.
  • the marker compounds without non-cyclic ester groups still function within the methods herein.
  • the select marker compound is first added to a fuel performance additive, such as a gasoline or diesel performance additive.
  • additives may include select amounts of detergents, antioxidants, carrier fluids, metal deactivators, corrosion inhibitors, biocides, antistatic additives, drag reducing agents, demulsifiers, emulsifiers, dehazers, anti-icing additives, antiknock additives, anti-valve-seat recession additives, lubricity additives, surfactants, combustion improvers, or combinations thereof.
  • the fuel performance additive may include about 1 to about 100 ppm of the marker compound, in other approaches, about 0.1 to about 75 ppm of the marker compound, or about 1 to about 50 ppm of the marker compound. [00020]
  • the fuels herein may include about 1 to about 5000 ppm of the fuel performance additive package with the marker compound therein.
  • the fuel may include up to about 4000 ppm, up to about 3000 ppm, up to about 2000 ppm, up to about 1000 ppm, up to about 900 ppm, up to about 800 ppm, up to about 600 ppm, up to about 550 ppm, up to about 400 ppm, up to about 200 ppm, up to about 150 ppm, up to about 100, ppm, up to about 60 ppm, up to about 50 ppm, or up to about 30 ppm of the fuel performance additive package.
  • the fuel may also include at least about 20 ppm of the fuel performance additive package, or at least about 40 ppm, at least about 70 ppm, at least about 90 ppm, at least about 150 ppm, at least about 200 ppm, at least about 300 ppm, at least about 400 ppm, at least about 450 ppm, at least about 500 ppm, at least about 900 ppm, at least about 1500 ppm, or at least about 2000 ppm.
  • the fuel performance additive package including the marker compound may be blended with the desired fuel source. [00021] When the hydrocarbon fuel is desired to be analyzed or identified, a sample of the fuel is taken.
  • the amount of fuel in the test sample is not particularly limited, but is usually less than about 100 ml, such as about 2 to about 25 ml of fuel, or about 2 to about 10 ml of the fuel to be analyzed.
  • the fuel is then combined with water by either adding the fuel to the water or, alternatively, adding water to the fuel to form a fuel and water mixture.
  • the amount of water used is about 1 to about 5 ml, or preferably, about 1 to about 3 ml of water.
  • water may be added in a lower amount than the fuel, which may increase the concentration of the marker compound in the water phase. In some approaches, the ratio of fuel to water is about 5:1 to about 1:1.
  • the ratio may be about 1:1 to about 3.5:1 (or 1:1 to about 3:1 or about 3:1) and for diesel, the ratio may be 1:1 to about 3:1 (or 1:1 to about 2.6:1 or about 2.6:1).
  • gasoline including ethanol some of the ethanol added to or included with the gasoline may enter the water phase, thus increasing the total volume of that phase.
  • water may be a distilled or deionized water or, optionally, a buffered water solution, such as pH 4 to 10 buffer solutions (in other approaches, a pH 6 to 8 buffer solution).
  • the buffer solution may be a 0.05 molar, pH 7 dihydrogen potassium phosphate and sodium phosphate dibasic buffer solution.
  • the fuel and water mixture is gently mixed, shaken, or agitated.
  • the mixture is then allowed to separate into a water and a fuel phase.
  • the water phase is analyzed within an appropriate container or vessel, such as a 10 mm NMR tube for instance (but any suitable glass or clear walled tube or container may be used).
  • Suitable gentle mixing, shaking, or agitation may be accomplished by gently shaking for about 30 seconds to about 2 minutes, or simply by inverting the NMR tube (or other container) 8 to 30 times, preferably 15 to 25 times, and most preferably, 20 times; however, other comparable gentle mixing procedures may be used.
  • the mixture is allowed sit for a period of time so that the mixture may again separate into fuel and water phases.
  • the mixture is allowed to sit and separate for about 1 to about 15 minutes, about 2 to about 10 minutes, or about 3 to about 5 minutes.
  • the select marker compounds herein are at least partially extracted or at least partially partitioned into the water phase.
  • the color bodies typically found in commercial gasoline or diesel fuels do not partition into the water phase, but remain in the fuel phase. Thus, any additives or other compounds in gasoline or diesel would not interfere with the water phase fluorescence.
  • a partition ratio of the marker compound between the water and the fuel phases herein may be at least about 0.1, at least about 0.2, at least about 0.3 at least about 0.4, at least about 0.5, at least about 1, at least about 2, at least about 5, at least about 8, at least about 10, at least about 15, or even at least about 20 and less than 30, less than 25, less than 20, less than 15, or even less than 10.
  • Partition ratios greater than 1 mean the marker compound is more soluble in water than fuel and partition ratios less than one mean the marker compound is partially soluble in water.
  • Fluorescence measurements may be conducted using a Perkin Elmer 204-a Fluorescence Spectrophotometer equipped with a tungsten-halogen light source. However, other suitable spectrophotometers may also be used. In approaches of the methods herein, the spectrophotometer was operated with slit widths set to about 10 mm for both excitation and emission wavelengths. If needed, an initial fluorescence intensity of the water before mixing and separation may be performed to determine any background noise or background fluorescence of the water used in the testing. Excitation wavelengths for the testing may range from about 250 nm to about 800 nm and may vary depending on the selected marker compound. Emission wavelength for the testing may range from about 300 nm to about 900 nm and may also vary depending on the selected marker compound.
  • marker compound of Formula 1 may have an excitation wavelength of 450 to 480 nm and preferably 470 nm and an emission wavelength of about 500 to about 550 nm and preferably 515 nm.
  • the marker compound of Formula II may have an excitation wavelength of 520 to 560 nm and preferably 540 nm and an emission wavelength of about 580 to about 660 nm and preferably 590 nm.
  • the marker compound of Formula III may have an excitation wavelength of 530 to 550 nm and preferably 540 nm and an emission wavelength of about 580 to about 600 nm and preferably 590 nm.
  • the spectrophotometer reports the fluorescence intensity, which those of ordinary skill appreciate is an arbitrary unit of measure reported from the instrument. From the measured fluorescence intensity, the concentration of marker compound (and thus the concentration of fuel performance additive) in the fuel can be determined because the concentration of the marker compound in the fuel (and thus, the amount of fuel performance additive in the fuel) is directly proportional to the fluorescence intensity (and preferably a linear relationship) within the concentration range of interest within the fuel. The identity of the hydrocarbon fuel can then be confirmed by ascertaining if the concentration of the fuel performance additive is within specification.
  • Hydrocarbon Fuels The hydrocarbon fuels of the present application may be applicable to the operation of diesel, jet, or gasoline engines.
  • the marker compounds herein are well suited for diesel or gasoline and, particularly, gasoline, and even more particularly, gasoline having an amount of ethanol therein.
  • the fuel is gasoline and, in another embodiment, gasoline having ethanol therein. In other another embodiment, the fuel is a diesel.
  • the fuels may include any and all middle distillate fuels, diesel fuels, biorenewable fuels, biodiesel fuel, fatty acid alkyl ester, gas-to-liquid (GTL) fuels, gasoline, jet fuel, alcohols, ethers, kerosene, low sulfur fuels, synthetic fuels, such as Fischer- Tropsch fuels, liquid petroleum gas, bunker oils, coal to liquid (CTL) fuels, biomass to liquid (BTL) fuels, high asphaltene fuels, fuels derived from coal (natural, cleaned, and petcoke), genetically engineered biofuels and crops and extracts therefrom, and natural gas.
  • GTL gas-to-liquid
  • gasoline jet fuel
  • alcohols alcohols
  • ethers ethers
  • kerosene low sulfur fuels
  • synthetic fuels such as Fischer- Tropsch fuels, liquid petroleum gas, bunker oils, coal to liquid (CTL) fuels, biomass to liquid (BTL) fuels, high asphaltene fuels, fuels derived from coal (natural
  • the biorenewable fuel can comprise monohydroxy alcohols, such as those comprising from 1 to about 5 carbon atoms.
  • suitable monohydroxy alcohols include methanol, ethanol, propanol, n-butanol, isobutanol, t-butyl alcohol, amyl alcohol, isoamyl alcohol, and mixtures thereof.
  • Preferred fuels include gasoline fuels.
  • the methods herein are particularly suited for use on alcohol-blended fuels, such as a fuel, gasoline, blended with ethanol.
  • a common ethanol-blended fuel is E10, which is a blend of 10 volume % ethanol and 90 volume % gasoline.
  • the fuels may include amounts of ethanol as described above.
  • Other ethanol based fuels may include, for example 85 volume % ethanol (E85), 50 volume % ethanol (E50), or 100 volume % ethanol (E100).
  • E10, gasoline, and diesel are seasonally adjusted to ensure proper starting and performance in different geographic locations.
  • the fuels herein are suitable for use in various internal combustion systems or engines.
  • the systems or engines may include both stationary engines (e.g., engines used in electrical power generation installations, in pumping stations, etc.) and ambulatory engines (e.g., engines used as prime movers in automobiles, trucks, road-grading equipment, military vehicles, etc.).
  • stationary engines e.g., engines used in electrical power generation installations, in pumping stations, etc.
  • ambulatory engines e.g., engines used as prime movers in automobiles, trucks, road-grading equipment, military vehicles, etc.
  • combustion system or engine herein is meant, internal combustion engines, for example and not by limitation, Atkinson cycle engines, rotary engines, spray guided, wall guided, and the combined wall/spray guided direct injection gasoline (“DIG” or “GDI”) engines, turbocharged DIG engines, supercharged DIG engines, homogeneous combustion DIG engines, homogeneous/stratified DIG engines, DIG engines outfitted with piezoinjectors with capability of multiple fuel pulses per injection, DIG engines with EGR, DIG engines with a lean-NOx trap, DIG engines with a lean-NOx catalyst, DIG engines with SN-CR NOx control, DIG engines with exhaust diesel fuel after-injection (post combustion) for NOx control, DIG engines outfitted for flex fuel operation (for example, gasoline, ethanol, methanol, biofuels, synthetic fuels, natural gas, liquefied petroleum gas (LPG), and mixtures thereof.) Also included are conventional and advanced port-fueled internal combustion engines, with and without advanced exhaust after- treatment systems
  • the base hydrocarbon fuel may contain an additive package or concentrate including one or more optional fuel additives.
  • the additive packages herein and/or the fuels may contain conventional quantities of detergents, cetane improvers, octane improvers, corrosion inhibitors, cold flow improvers (CFPP additive), pour point depressants, solvents, demulsifiers, lubricity additives, friction modifiers, amine stabilizers, combustion improvers, dispersants, antioxidants, heat stabilizers, conductivity improvers, metal deactivators, marker dyes, organic nitrate ignition accelerators, cycloaromatic manganese tricarbonyl compounds, carrier fluids, antifoam agents, and the like appropriate for the type of fuel.
  • CFPP additive cold flow improvers
  • pour point depressants solvents
  • demulsifiers demulsifiers
  • lubricity additives friction modifiers
  • amine stabilizers combustion improvers
  • dispersants antioxidants
  • heat stabilizers conductivity improvers
  • metal deactivators marker dyes
  • organic nitrate ignition accelerators cycloaro
  • compositions described herein may contain about 10 weight percent or less, or in other aspects, about 5 weight percent or less, based on the total weight of the additive package or concentrate, of one or more of the above additives.
  • the fuels may contain suitable amounts of conventional fuel blending components such as methanol, ethanol, butanol, dialkyl ethers, 2-ethylhexanol, fatty acid methyl esters (FAME, biodiesel) and the like. If used, the fuel preferably includes at least about 1 volume percent of such fuel blending components, and in other embodiments, about 2 to about 20 volume percent, or about 2 to about 15 volume percent, or about 2 to about 10 volume percent. In some approaches, the fuel blending component is ethanol.
  • organic nitrate ignition accelerators that include aliphatic or cycloaliphatic nitrates in which the aliphatic or cycloaliphatic group is saturated, and that contain up to about 12 carbons may be used.
  • organic nitrate ignition accelerators examples include methyl nitrate, ethyl nitrate, propyl nitrate, isopropyl nitrate, allyl nitrate, butyl nitrate, isobutyl nitrate, sec-butyl nitrate, tert-butyl nitrate, amyl nitrate, isoamyl nitrate, 2-amyl nitrate, 3-amyl nitrate, hexyl nitrate, heptyl nitrate, 2-heptyl nitrate, octyl nitrate, isooctyl nitrate, 2-ethylhexyl nitrate, nonyl nitrate, decyl nitrate, undecyl nitrate, dodecyl nitrate, cyclopentyl nitrate, cyclohexyl
  • metal deactivators useful in the compositions of the present application are disclosed in US 4,482,357, the disclosure of which is herein incorporated by reference in its entirety.
  • metal deactivators include, for example, salicylidene-o- aminophenol, disalicylidene ethylenediamine, disalicylidene propylenediamine, and N,N′- disalicylidene-1,2-diaminopropane.
  • Suitable optional cycloaromatic manganese tricarbonyl compounds which may be employed in the compositions of the present application include, for example, cyclopentadienyl manganese tricarbonyl, methylcyclopentadienyl manganese tricarbonyl, indenyl manganese tricarbonyl, and ethylcyclopentadienyl manganese tricarbonyl.
  • cyclopentadienyl manganese tricarbonyl methylcyclopentadienyl manganese tricarbonyl
  • indenyl manganese tricarbonyl and ethylcyclopentadienyl manganese tricarbonyl.
  • ethylcyclopentadienyl manganese tricarbonyl ethylcyclopentadienyl manganese tricarbonyl.
  • Suitable detergents include but are not limited to succinimides, Mannich base detergents, quaternary ammonium compounds, bis-aminotriazole detergents as generally described in US 8,529,643; US 2012/0010112; and/or US 10,308,888 (which are all incorporated herein by reference), or a reaction product of a hydrocarbyl substituted dicarboxylic acid, or anhydride and an aminoguanidine, wherein the reaction product has less than one equivalent of amino triazole group per molecule as generally described in US 8,758,456 and/or US 8,852,297, which are both incorporated herein by reference.
  • the detergent is selected from the group consisting of Mannich reaction products formed by condensing a long-chain aliphatic hydrocarbon-substituted phenol or cresol with an aldehyde and an amine; long chain aliphatic hydrocarbons having an amine or a polyamine attached thereto; fuel-soluble nitrogen containing salts, amides, imides, succinimides, imidazolines, esters, and long chain aliphatic hydrocarbon-substituted dicarboxylic acids or their anhydrides or mixtures thereof; polyetheramines; and combinations thereof.
  • Suitable carrier fluids may be selected from any suitable carrier fluid that is compatible with the gasoline and is capable of dissolving or dispersing the components of the additive concentrate.
  • the carrier fluid is a hydrocarbyl polyether or a hydrocarbon fluid, for example a petroleum or synthetic lubricating oil basestock including mineral oil, synthetic oils such as polyesters or polyethers or other polyols, or hydrocracked or hydroisomerised basestock.
  • the carrier fluid may be a distillate boiling in the gasoline range.
  • the amount of carrier fluid contained in the additive concentrate may range from 10 to 80 wt. %, or from 20 to 75 wt. %, or from 30 to 60 wt. % based on a total weight of the additive concentrate.
  • additives of the present application including the marker compounds as described above, and any optional additives used in formulating the fuels of this disclosure may be blended into the base fuel individually or in various sub-combinations.
  • the marker compounds of the present application may be blended into the fuel concurrently using an additive concentrate, as this takes advantage of the mutual compatibility and convenience afforded by the combination of ingredients when in the form of an additive concentrate.
  • the marker compound is first blended with the fuel performance additive or concentrate, which is then blended into the fuel. Also, use of a concentrate may reduce blending time and lessen the possibility of blending errors.
  • hydrocarbyl substituent or “hydrocarbyl group” is used in its ordinary sense, which is well-known to those skilled in the art. Specifically, it refers to a group having a carbon atom directly attached to the remainder of the molecule and having a predominantly hydrocarbon character.
  • Each hydrocarbyl group is independently selected from hydrocarbon substituents, and substituted hydrocarbon substituents containing one or more of halo groups, hydroxyl groups, alkoxy groups, mercapto groups, nitro groups, nitroso groups, amino groups, pyridyl groups, furyl groups, imidazolyl groups, oxygen and nitrogen, and wherein no more than two non-hydrocarbon substituents are present for every ten carbon atoms in the hydrocarbyl group.
  • percent by weight or “wt%”, unless expressly stated otherwise, means the percentage the recited component represents to the weight of the entire composition.
  • alkyl if uesd herein, unless specified otherwise, refers to straight, branched, cyclic, and/or substituted saturated chain moieties of from about 1 to about 200 carbon atoms.
  • alkenyl if used herein, unless specified otherwise, refers to straight, branched, cyclic, and/or substituted unsaturated chain moieties of from about 3 to about 30 carbon atoms.
  • aryl if used herein, unless specified otherwise, refers to single and multi- ring aromatic compounds that may include alkyl, alkenyl, alkylaryl, amino, hydroxyl, alkoxy, halo substituents, and/or heteroatoms including, but not limited to, nitrogen, and oxygen.
  • the “molecular weight” or “MW” if used herein, unless specified otherwise, is determined by gel permeation chromatography (GPC) using commercially available polystyrene standards (with a Mn of 180 to about 18,000 as the calibration reference).
  • GPC gel permeation chromatography
  • EXAMPLE 1 the fluorescence of various unmodified marker compounds were evaluated.
  • the general protocol involved obtaining a measured amount of fuel treated with an additive package with a fluorescent marker therein was first dispensed into a clear glass vial. Then, a measured amount of distilled water or buffered water solution as noted below was added to the vial. The vial with gently agitated (inverted 20 times) to mix the water and fuel.
  • the diesel used in the examples was No.2 ultra-low sulfur diesel fuel and was obtained from the same terminal.
  • Fluorescence measurements were made with a Perkin Elmer 204-A Fluorescence Spectrophotometer equipped with a tungsten-halogen light source. Slit widths were set to 10 mm for both the excitation and emission wavelengths. The sample vial was arranged in the instrument such that the excitation beam passed only through the water (lower) phase.
  • Gasoline additive base composition (Blend 1): The detergent in Blend 1 was a Mannich reaction product of a 1000 Mn polyisobutylene substituted cresol reacted with formaldehyde and an amine. [00051] Table 2. Diesel additive base composition (Blend 2): The detergent in Blend 2 was a quaternary ammonium additive synthesized according to the procedure given for Preparation Example 1 in US 2012/0010112 A1. [00052] Blend 1 or Blend 2 was combined with a base fuel (gasoline or diesel) according to the amounts in Table 3 and Table 4 below. [00053] Table 3.
  • FIGS.1 to 5 The data from the table 4 is plotted in FIGS.1 to 5 showing the linear correlations between the fluorescence intensity of the water layer relative to the treat rate of the additive composition in the fuel.
  • EXAMPLE 2 [00058] In this Example, the separation/partition of the marker compound between water and fuel phases was measured. The procedure for this Example included: measure fluorescence of 10 grams of water phase with and without marker compound present to determine background fluorescence. Then, 10 grams of hydrocarbon including 10 ppb of marker compound was added to the water and gently agitated for 1 minute. After mixing, the sample was allowed to completely separate into two phases. Thereafter, the fluorescence of the water phase was re- measured.
  • the Partition Ratio can be calculated from the initial and final tracer fluorescence intensities (corrected for any background fluorescence) from the water phase.
  • Rhodamine B, Rhodamine 101, and Fluorescein marker compounds were used.
  • excitation wavelength was 540 nm and emission wavelength was 590 nm.
  • Fluorescein measurements excitation wavelength was 470 nm and emission wavelength was 515 nm. The measured fluorescence and partition ratio is shown in Table 5 below.
  • the intensity in the water phase after extraction tends to be proportional to the concentration of the marker in the fuel, intensity of the instrument’s excitation wavelength, the sensitivity of the instrument’s detector to the emission wavelength, the absorbance of the tracer to the excitation wavelength, and/or the fluorescence quantum yield as well as the water/gasoline partition ratio.
  • each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.
  • each component, compound, substituent or parameter disclosed herein is to be interpreted as being disclosed for use alone or in combination with one or more of each and every other component, compound, substituent or parameter disclosed herein.
  • each range disclosed herein is to be interpreted as a disclosure of each specific value within the disclosed range that has the same number of significant digits.
  • a range from 1 to 4 is to be interpreted as an express disclosure of the values 1, 2, 3 and 4 as well as any range of such values.
  • each lower limit of each range disclosed herein is to be interpreted as disclosed in combination with each upper limit of each range and each specific value within each range disclosed herein for the same component, compounds, substituent or parameter.
  • this disclosure to be interpreted as a disclosure of all ranges derived by combining each lower limit of each range with each upper limit of each range or with each specific value within each range, or by combining each upper limit of each range with each specific value within each range. That is, it is also further understood that any range between the endpoint values within the broad range is also discussed herein.
  • a range from 1 to 4 also means a range from 1 to 3, 1 to 2, 2 to 4, 2 to 3, and so forth.
  • specific amounts/values of a component, compound, substituent or parameter disclosed in the description or an example is to be interpreted as a disclosure of either a lower or an upper limit of a range and thus can be combined with any other lower or upper limit of a range or specific amount/value for the same component, compound, substituent or parameter disclosed elsewhere in the application to form a range for that component, compound, substituent or parameter.
  • While particular embodiments have been described, alternatives, modifications, variations, improvements, and substantial equivalents that are or can be presently unforeseen can arise to applicants or others skilled in the art. Accordingly, the appended claims as filed and as they can be amended are intended to embrace all such alternatives, modifications variations, improvements, and substantial equivalents.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Immunology (AREA)
  • General Health & Medical Sciences (AREA)
  • Analytical Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Biochemistry (AREA)
  • Pathology (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Emergency Medicine (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Molecular Biology (AREA)
  • Optics & Photonics (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

Abstract

La présente divulgation concerne des procédés d'identification d'un carburant hydrocarboné, tels que la présence et/ou les quantités de composés marqueurs ayant une intensité de fluorescence et, par corrélation, la présence et/ou les quantités d'une ou plusieurs préformulations d'additifs dans le carburant hydrocarboné.
EP21815074.6A 2020-11-02 2021-10-28 Procédés d'identification de carburant d'hydrocarbures Pending EP4237847A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US17/087,127 US20220136968A1 (en) 2020-11-02 2020-11-02 Methods of identifying a hydrocarbon fuel
PCT/US2021/072073 WO2022094572A1 (fr) 2020-11-02 2021-10-28 Procédés d'identification de carburant d'hydrocarbures

Publications (1)

Publication Number Publication Date
EP4237847A1 true EP4237847A1 (fr) 2023-09-06

Family

ID=78771261

Family Applications (1)

Application Number Title Priority Date Filing Date
EP21815074.6A Pending EP4237847A1 (fr) 2020-11-02 2021-10-28 Procédés d'identification de carburant d'hydrocarbures

Country Status (5)

Country Link
US (1) US20220136968A1 (fr)
EP (1) EP4237847A1 (fr)
CN (1) CN116648495A (fr)
MX (1) MX2023005133A (fr)
WO (1) WO2022094572A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20230384210A1 (en) * 2022-05-31 2023-11-30 Saudi Arabian Oil Company Method to Detect Diesel in Fluid Samples

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB361310A (en) * 1930-06-18 1931-11-18 Howard Ferguson Improvements in and relating to motor fuels or like combustible liquids
US3015668A (en) 1959-11-24 1962-01-02 Ethyl Corp Process for producing cyclomatic manganese tricarbonyl compounds
US4482357A (en) 1983-12-30 1984-11-13 Ethyl Corporation Fuel Compositions
GB2239258A (en) 1989-12-22 1991-06-26 Ethyl Petroleum Additives Ltd Diesel fuel compositions containing a manganese tricarbonyl
US5358873A (en) * 1992-07-27 1994-10-25 Atlantic Richfield Company Method for determining adulteration of gasolines
GB9500816D0 (en) * 1995-01-17 1995-03-08 Exxon Chemical Patents Inc Fuel oil compositions
WO1996032462A1 (fr) * 1995-04-13 1996-10-17 United Color Manufacturing, Inc. Marqueurs de petrole incolores
WO2002004431A1 (fr) * 2000-07-12 2002-01-17 Sk Corporation Marqueur silencieux pour produit petrolier et procede de detection dudit marqueur
US6514917B1 (en) * 2001-08-28 2003-02-04 United Color Manufacturing, Inc. Molecular tags for organic solvent systems
US8529643B2 (en) 2008-05-13 2013-09-10 Afton Chemical Corporation Fuel additives for treating internal deposits of fuel injectors
US20090319195A1 (en) * 2008-06-20 2009-12-24 Hoots John E Method of monitoring and optimizing additive concentration in fuel ethanol
GB0813277D0 (en) * 2008-07-18 2008-08-27 Lux Innovate Ltd Method to assess multiphase fluid compositions
US20120010112A1 (en) 2010-07-06 2012-01-12 Basf Se Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
SG184591A1 (en) * 2011-03-16 2012-10-30 Decipher Pte Ltd Kit for marking and/or detecting alteration of fueland its method thereof
US8758456B2 (en) 2011-09-22 2014-06-24 Afton Chemical Corporation Fuel additive for improved performance of low sulfur diesel fuels
US8852297B2 (en) 2011-09-22 2014-10-07 Afton Chemical Corporation Fuel additives for treating internal deposits of fuel injectors
US10308888B1 (en) 2018-06-15 2019-06-04 Afton Chemical Corporation Quaternary ammonium fuel additives

Also Published As

Publication number Publication date
US20220136968A1 (en) 2022-05-05
MX2023005133A (es) 2023-08-04
CN116648495A (zh) 2023-08-25
WO2022094572A1 (fr) 2022-05-05

Similar Documents

Publication Publication Date Title
US9562498B2 (en) Biodegradable fuel performance additives
Amaral et al. Effects of gasoline composition on engine performance, exhaust gases and operational costs
WO2007020234A1 (fr) Compositions de carburant
CA2672199A1 (fr) Composition de carburant sans plomb et son utilisation
EP3464521A1 (fr) Compositions de carburant
EP2582777B1 (fr) Composition de carburant et son utilisation
US20220136968A1 (en) Methods of identifying a hydrocarbon fuel
US9447356B2 (en) Diesel fuel with improved ignition characteristics
US9222047B2 (en) Liquid fuel compositions
US9862905B2 (en) Diesel fuel with improved ignition characteristics
Patil et al. Literature review on need of composite additives for SI Engine
US11084997B2 (en) Process for preparing a diesel fuel composition
Kumar et al. Study of performance and emission characteristics of propan-2-ol and gasoline fuel blends in an unmodified spark ignition engine
RU2161639C1 (ru) Добавка к бензину и композиция, ее содержащая
RU2148077C1 (ru) Добавка к бензину и композиция, ее содержащая
WO2018077976A1 (fr) Procédé de préparation d'un gazole automobile
Fadel et al. Chemical Methodologies
EP3184612A1 (fr) Procédé de préparation d'une composition de carburant diesel
AU2020273616A1 (en) Compositions and methods and uses relating thereto
BR112020020962B1 (pt) Uso de um agente de expansão
JP2011127083A (ja) マルチグレード軽油燃料組成物
UA55879A (uk) Композиційна добавка до автомобільних палив

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: UNKNOWN

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20230516

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

RIN1 Information on inventor provided before grant (corrected)

Inventor name: ANDERSON, DANA

Inventor name: SCHWAB, SCOTT D.

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

17Q First examination report despatched

Effective date: 20240613